


Peeping Fox

by The_Anxious_Salad



Category: Sonic Boom (Cartoon), Sonic the Hedgehog (Video Games), Sonic the Hedgehog - All Media Types
Genre: Accidental Voyeurism, Amy is the only person genderbent in this story, Anal Sex, Dirty Talk, Forced Crossdressing, Genderbending, Humiliation, Jealousy, M/M, Non-Consensual Spanking, One-Sided Attraction, Oral Sex, Rough Oral Sex, Shameless Smut, Smut, Somewhat wholesome?, Spanking, maid outfit
Language: English
Status: Completed
Published: 2021-03-14
Updated: 2021-03-14
Packaged: 2021-03-22 21:01:02
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,288
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30044673
Author URL: https://archiveofourown.org/users/The_Anxious_Salad/pseuds/The_Anxious_Salad
Summary: Tails ends up in Jamie's (Amy) closet after making a teleporter and sees some things he wasn't supposed to see. After invading his friend's privacy he's understandably too afraid to face him and apologize. Jamie, being very upset asks of him to do very questionable things to blackmail Tails to prevent him from telling Sonic about what he's seen.One of those things involves putting him in a maid outfit.Cause that's what friends are for right?
Relationships: Amy Rose & Miles "Tails" Prower, Amy Rose & Sonic the Hedgehog, Amy Rose/Miles "Tails" Prower, Miles "Tails" Prower & Sonic the Hedgehog





	Peeping Fox

**Author's Note:**

  * For [My yellowpissfriend](https://archiveofourown.org/gifts?recipient=My+yellowpissfriend).



> Wow, my first fanfic I post here and it's...this. Uh...yeah.
> 
> This goes out to that one weirdo who forced me to make this by keeping me and my family hostage.
> 
> The headcanon look of genderbent Amy (or Jamie Rose for that matter) in this fic was inspired by KayeScribbles amazing art: https://www.deviantart.com/kayescribbles/art/Genderbent-Boom-Amy-612763569

It was late into the night as Tails inhabited his workshop. The days throughout the weeks were abnormally quiet. They haven’t seen Eggman for quite some time, which means the gang hasn’t met up in a while.

They were off doing their own thing, and rarely visiting Tails. Only Sonic was passing by his hut or workshop once or twice a day before speeding off somewhere. So Tails had nothing to do except for work on his own inventions, which he didn’t mind, though it did get lonely sometimes.

Still he didn’t linger on his thoughts for too long, he did appreciate Sonic always checking on him even though he’d seemed less interested in hanging around him. He wished that wasn’t the case, but it didn’t seem like he had much of a say in it.

Tails just decided to occupy his mind with tinkering on his newest contraption. It was supposed to transport atoms to separate locations, all he needed was a receiving end to it so he could transport them wherever he wanted.

He decided to make it solely because he needed a way to safely disregard any nuclear waste from his nuclear generator. Perhaps there was a better way to dispose of this but his boredom had gotten the better of him.

He worked from 6AM to 9PM with only a few short breaks, it was when his hands started to cramp when he had decided to call it for the night. He sat back against his spinning chair, reaching his arms above his head to stretch and yawn as long as he could.

His fangs glinted in the dim overhanging light of his workshop before he removed his goggles from his face by lowering them to his neck. He pushed around his empty mug of what once was hot coffee for a bit since he needed something mindless to do before beginning to rise to his feet.

He looked back at the transporter he’d been dedicating his whole day to and smiled at it with satisfaction. Perhaps he should give it another test run before heading to bed.

He couldn’t remember the last time he had tested it out but he didn’t receive any significant results, so it was wise to see whatever components he was still missing with it. He grabbed his contraption and laid it flat onto his working table. Starting this up he searched around a bit, looking for an object to test it on.

It took him a second or two to find the nearest thing close to him which was an apple core he had earlier.

He dropped it on top of the plate-like machine and just within an instant it had disappeared.

“Nice.” He said to himself quietly and chuckling a bit before searching around for his notepad to record his progress.

He wondered where the apple must’ve gone, but it could literally be anywhere without the receiver. Tails turned his back, looking around his disorganized workspace. Man he really needed to clean up or something, maybe he could get Sonic to help him. As his mind was consumed with thoughts about making plans with Sonic, he didn’t notice one of his twin tails was absentmindedly brushing against the transporter. He didn’t realize this until it was too late. 

_Oh no-_

His body had started vibrating unexpectedly, and his workshop and the floor below him had started to disappear.

He felt his entire body being scrambled before his feet had quickly touched the solid ground once again. His legs had given up under his weight, making him collapse to the ground.

Tails’ head felt a whirlwind of pain once he had fallen face first. He laid there completely still for a few moments until he no longer felt dizzy, his eyes blinking rapidly.

He groaned for a bit as he lifted his head, taking in his surroundings. Based on the wooden walls, straw roof and open windows he was in a hut.

Which was good since he didn’t end up in the middle of the ocean or worse...space.

Judging by the artwork on the walls, the historic artifacts and that long purple couch in the living space; not to mention the evasive smell of black cherry incense pervading through the air, he could tell he was in Jamie’s house. Tails’ fur bristled at the sound of footsteps thudding against the wooden flooring. 

Impulsively he shot straight behind the couch, wincing as he had almost knocked over a pillar but quickly saved it by moving it upright again with his foot. Wrapping both of his tails over his body and tucking into a small ball, he'd peeked through the gap of Jamie’s couch. 

His heart was in his throat, watching with wide eyes as the pink hedgehog’s feet stopped directly in the center of the room and walked back and forth a few times before exiting.

A soft sigh of relief blew past his lips, he waited a second or two before standing up and hurriedly made his way toward the front door. However the sound of footsteps alerted Tails and made him impulsively hide in the closest location he could find, that being Jamie’s room which was probably not the best idea but there were no other options.

He immediately hid in Jamie’s closet and sank further behind his hung clothes as he heard the footsteps approaching, his teeth gritting as he hoped Jamie wouldn’t find him. 

He heard the hedgehog mutter something indistinguishable to himself as he entered the bedroom. Tails could see through the door, the shape of the hedgehog immediately undressing, which made Tails’ heart leap right out of his chest.

He averted his eyes, though he didn’t know why exactly. He’s seen Jamie without a vest on a million of times. Maybe it had to do with how intimate in and wrong it was in this setting.

The hedgehog started untangling his bandages, gloves and shoes before lounging in the nude. Browsing through his laptop.

 _Oh great…_ Who knew how long he’d be stuck here until Jamie decided to fall asleep. And by the look of Jamie's face he didn't look tired at all. Starting his binge through those awful romantic drama shows with a hopeful expression. Tails is gonna be in here for weeks...

He fought back an annoyed groan from his throat and forced himself to not fidget. His attention to detail heightened in order to occupy his mind with something, every shift in position Jamie made and every sound and or comment to himself.

It felt like an eternity before the sounds of the laptop stopped and it shut as he put it aside on his night stand. Tails’ was on the verge of falling asleep but Jamie gained his attention as he had let out a muffled yawn. 

_He was getting tired!_

Perfect, he’ll be home in no time.

He looked expectantly through the door, however his pink friend didn’t turn off the lights or anything.

Instead he had bent over the opposite side of his bed, away from the closet which made it hard for Tails to see what his friend was doing. It took a few seconds before Tails had spotted something blue as he held it tightly against his chest.

_Wait is that a doll? Of Sonic...?_

Tails’ eyes widened and he quickly threw his hand over his mouth to silence himself from laughing. _Oh this was rich…_

He couldn’t believe Jamie had a literal plush doll of Sonic, he always knew that Jamie had a bit of a crush on Sonic, but this was just straight up sad. Like why on Earth would Sonic like him?! Sonic wasn’t interested in anybody.

 _But if he was, he’d definitely be interested in me!_ Tails didn’t bother reflecting on the sudden defensiveness of the idea of Sonic rather being interested in him, and stuck to just shamelessly making fun of Jamie in his head.

"You're always there to love and support me Sonic." Jamie said softly as he hugged the doll tightly.

A few sounds came out from the yellow fox which he tried his hardest not to let out. His chest hurt as he tried to keep in his laughter. He shut his eyes, doubling over for a few seconds to control himself.

Through watery eyes, he looked up again and noticed something off.

Jamie was now talking softly to the doll, which was creepy but it became even more creepy as the pink hedgehog pulled out his erect penis.

Tails’ heart was in his throat again, his chest moving rapidly as his face flushed from embarrassment. This went from hilariously sad, to straight up weird.

Jamie had kissed the doll in it's supposed mouth while he stroked himself. "Oh Sonic." The pink hedgehog moaned Sonic's name which the longer Tails watched, the more he felt utterly terrified.

He felt like such a criminal spying on his friend jacking off. Such a violation to his privacy. Tearing away his eyes from the pink hedgehog as he stroked himself firmly, Tails tried not to focus on his pulsating body. Jamie’s voice softly repeated Sonic’s name more. The louder he was the longer this went off the more lewded his moans had become as his voice shook, making Tails’ throat feel dry.

_So hot..._

Tails managed to snap himself away from any more thoughts about his friend in a sexual light and contemplated booking off. He frantically shot his hands forward to close the door so he couldn't see anymore. Which in exchange made the fox fall forwards, straight against the door thus opening it. Making a loud sound as he thudded onto the floor in the process.

Tails felt his blood run cold as soon as the room had gone dead silent. Tails dared to look up at Jamie with his cock still in hand, his blue eyes wide and his face on fire as they kept eye contact.

“T-Tails?” Jamie’s voice was calm but confused. Though he looked flushed regardless, especially as he pathetically attempted to hide his doll of Sonic.

“I-I er uh-” Tails stuttered, he began scrambling to his feet. His eyes immediately landed on Jamie’s cock which made him blush with even more embarrassment. In a split second decision he ran out the door without a word. He could hear the shouting behind him as he ran out of Jamie’s house and didn’t dare to look back. He definitely didn’t think about how big his dick was on the way home either. He just rushed to his room and hid himself under the covers, trying to forget everything that had occurred. 

He's not gonna sleep well tonight.

***

“Come on Tails, I really don’t want to help Jamie out with redecorating his house again.” Sonic groaned as he tried to convince Tails to go visit Jamie’s house. Tails ignored Sonic hanging over him as he finally did the finishing touches of his receiver. His mouth in a tight scowl as he avoided looking up. Though Sonic had continued, “And he said he didn’t mind you helping out. He actually seemed like he really wanted your company.”

Tails’s eyes immediately reached Sonic’s as he looked apprehensively at him. “What did he tell you?!” Tails had immediately jumped to questioning.

It had been three days since the incident and he was paranoid about Jamie telling anybody that he found him in his closet spying on him.

He knew the likelihood of Jamie telling the others was unlikely since Tails had seen his doll of Sonic, though he didn’t quite know with Jamie. He was reasonable most of the time but he could be unpredictable at times. Especially when it comes to his status being at stake. His friends had seen him as the voice of reason and being absolutely perfect and right all the time. He'll go to the ends of the Earth to make sure nothing tarnishes his reputation.

Which only made Tails even more afraid and hesitant to even be around him.

So when Sonic had looked at him with wide and confused eyes, Tails avoided his gaze and looked back at his bench. His face glowing red with embarrassment.

"Are you..ok?" Sonic asked scratching the back of his quills uncomfortably.

“Yeah I'm fine.” He answered, taking a deep breath. "How much do you not want to go?" He asked, turning to face his blue friend.

"Tails, I would rather become paraplegic than visit Jamie." Sonic said, crossing his arms and looking pleadingly at him.

Tails sighed before nodding. "Alright…" Pushing himself away from the bench he could tell Sonic was giving a big goofy grin and a look of relief toward him. “Thanks man! I’m gonna go to Meh Burger with Knuckles and Sticks.”

The mention of Sonic doing something without him made the fox bristle, his teeth automatically grinding together with anger. Didn’t Sonic want to hang out with him instead?! Why was he trying to get rid of him? Sonic’s voice rose to Tails' ears once more. 

“Want me to bring you back something?” He offered but Tails had looked at Sonic and shoved past him. “No! Go have your stupid burgers without me!” He hissed with spite, storming out of his workshop and leaving Sonic looking at him confused before scoffing out loud.

“Yeesh, someone's on their period.”

Tails slammed the door shut, his lip trembling as he refused to let his tears swarm his vision. _Stupid Sonic…_ He thought angrily to himself, he hated how Sonic was so quick to disregard him nowadays now that they were older and becoming more independent. It wasn't fair.

He made his way to Jamie’s house, as slow as possible. Wanting to cool down a bit before heading over.

After a couple of minutes of walking he had instantly spotted the pink hedgehog watering the flowers outside of his house. He was in his casual outfit, purple vest and all, though the image of him completely naked was still stained in Tails' brain. Which he hated.

Jamie's humming went to a complete stop as his eyes had landed onto the fox who was just standing there. “Hey Tails.” He greeted him kindly. It almost seemed as if Tails had imagined what had happened that night. With the way how natural and placid Jamie seemed in the moment.

“Hey Jamie…” He greeted back softly, his gaze not meeting his.

The pink hedgehog swiped his tuft of quills away from his face as beads of sweat had fallen from them and onto his eyes. Tails decided to focus on his chest as he did this, though that wasn’t helping as much since he was reminded of _the night_ once more. Memories his fit chest moving up and down as he panted. His head had snapped up quickly as he had heard Jamie speak.

“I want to talk to you about something.” Tails met Jamie’s eyes for a second as he said this.

“S-Sure Jamie.” Tails growled as he scratched the back of his head.

Maybe he’ll receive another one of his famous lectures. This time about privacy or something which annoyed the hell out of him.

Jamie gestured to the fox toward his house and told him to sit on the couch, a whiplash of a new scent hit Tails’ nose as he entered the room, the smell was a mixture of vanilla and lavender. Interesting combination than his usual cherry or rose related incense.

Tails' jaw became lax the more he absorbed the scent, which was strange. He didn’t quite understand Jamie’s weird interest in aromatherapy, but it was surely something. It must work too if the scents that mixed together so well in the home made the fox's nerves feel at ease. Tails looked around the living area, taking note of the few packages laying around as he waited patiently on the comfy couch. He had heard Jamie in the kitchen and after a few moments he had approached the fox with two mugs. 

“Coffee with caramel creamer?” He asked as he handed it to him, Tails nodded in confirmation and took a sip. “Yeah- wait how do you know?” He licked his lips from the sweetness. It was just right.

“I have my ways.” He said cryptically with a wink, making Tails feel as if ants were crawling up and down his spine.

 _Oh shit I’m being drugged._

Tails put down the mug, watching Jamie with wide eyes as he sat down right next to him and took a sip for himself. He needed to get out of here didn’t he- Jamie was mad at him- oh no-

“So Tails, about that night.” Jamie started as he placed his mug down.

Tails immediately cracked, tension swarming his body. “I’m sorry Jamie- I didn’t mean to-I just- you see how my transporter worked and I accidentally- please don’t steal my kidney-” He stuttered like a complete oaf.

“Tails, Tails.” Jamie chided softly which made the waterfall of words coming from Tails' mouth come to a complete halt. He managed to look at Jamie, his teeth clenching with fear.

“Don’t worry, I’m not mad or anything.” He chuckled and waved his hand dismissively. “Accidents happen.” He shrugged and took a long sip of his mug, which made the fox feel ten times better. “Haha...I thought you were gonna drug me and throw my body in the ocean...heh.”

“Drug you? Oh Tails.” He placed a gentle hand on Tails' shoulder and began laughing, which encouraged Tails own laughter.

He was so relieved Jamie wasn’t mad at him… Their laughs come to a halt which makes Tails feel comfortable enough to drink his coffee again, it was still a bit hot but drinkable. Not to mention the coffee complimented the room's aroma as well. He started to melt on top of the couch while cradling his mug close to his stomach and chest. Jamie watched him intently for a few seconds before speaking again. 

“You know however. There is one problem.”

Tails blinks for a second or two before removing his muzzle away from his mug before replying. “And...And what’s that?”

Jamie's fingers circle around the rim of his mug, turning his face away slightly. “Well...I know you’ve seen that doll I’ve had.” His tone darkened a bit as he said this which made Tails uneasy.

“Yeah...I’m sorry. I won’t tell anybody.” He said apologetically, though he still thought Jamie was a complete weirdo for making and keeping something like that and jerking off to it. Jamie spoke softly before taking a final sip out of his mug. “Oh I know you won’t tell anybody.” Jamie said in a normal tone while placing the mug on the table, finally staring at him he says. “Because you’re gonna repay me.”

Tails blinked and casted a look downwards at his cup, letting out a huff. He supposed that was the reason why he was even here in the first place. “Fine, you want me to redecorate your entire house right?” 

“Not just that.” Jamie said with a smile and while placing his elbow on his leg and holding up his head to look at Tails. Tails had assumed he wanted him to guess, but Tails couldn’t imagine what else he wanted from him. So the fox responds with a questioning look. “What else?"

“Be my servant for a month.”

Tails looked at him, quiet for a minute or two before his voice elevating with confusion. “W-What?!” His teeth started to grit once more. What kind of request was that?

Jamie had sat upright and stared at him with those green eyes as they were clouded with malice. “You wouldn’t want our friends or even the entire island to know you’re some peeping tom right?” Tails’ mouth gaped at his threat, his limbs shaking a bit as he thought about his friends finding out. It just wouldn’t look good on his end. Sonic would think so low of him if Jamie told him, and he couldn’t stand the thought of that happening. The fox swallowed hard, his brows furrowing with anger. 

“Okay.” He said curtly. 

Jamie clasped Tails' on the shoulder. “Great! You’ll do as I say?” Tails was hesitant to agree but did so anyways with a nod. “Great! Now before you get started, I need you to do something very important for me.” He said while standing up. Tails looked at him curiously but he had only held out one finger as he disappeared into his room.

It was a minute or two before Jamie had come out again but with a maid outfit. Though it was extremely suggestive, having an exposed back and extremely short skirt. Not to mention that stupid looking maid headband with a big black bow on top. Tails looked at it incredulously, drawing parallels as to what the hedgehog had said earlier. The yellow fox had begun shaking his head.

“No, no, no-” Jamie had smiled and handed the outfit to him. “Yes, yes, yes. Wear it.” He prompted, slipping his hands on the fox’s shoulder. “Now.” He commanded as Tails struggled to even look at the outfit directly.

He was starting to hate Jamie strongly. Tails stood, his balled up fist tightening against the clothing as he was heading toward the bathroom to change but Jamie snapped his fingers at him. 

“No, no, change here.”

Tails gave him a look as if to ask him if he was serious. But of course he was… Tails let out a loud groan before starting to slowly take off his belt and goggles, avoiding Jamie’s eyes from the shame. 

Yeah. 

He hated him.

***

Jamie watched with satisfaction as he watched the fox slip into the maid dress he bought exactly for him. It was great seeing the look of contempt on his face. That’d teach him not to intrude on his private sessions. 

He hated to admit that he still was bitter about Tails popping up unexpectedly in his bedroom, especially when he’d said all those embarrassing stuff about Sonic. He needed to feel that very same kind of humiliation he went through that night. Tails looked up at him expectantly with those cute blue round eyes. 

“I want you to replace that painting with this new one I just ordered.” He said pointing across the room. "You can play around with the room a bit, as you could probably see I'm trying something new with the living room. Going for a more...ancient rome vibe. So I trust your judgement." Jamie explained with a smile but then quickly added. "Well not completely trust, but it's better than any of our other friends." Tails just looked at him blankly, not taking what he said as a compliment before he had obeyed. His pace was sluggish as he made it across the room, his cute little paws made a thud with each step.

Things were almost perfect and just exactly as he had imagined, though he noticed Tails was intentionally using both of those pesky tails to shield Jamie’s view of his ass, which made Jamie a little irritated. He followed behind Tails closely as he had begun taking the artwork away from the wall while standing on a stool. It only took a few seconds before Tails finally snapped. “What is it?!”

Jamie looked at him with crossed arms. “Oh nothing." He said, clearly having more to say. 

"It's just I need you to start lifting your Tails up more.” He gave a toothy grin at him.

Tails froze, his eyes not meeting his gaze for a moment or two before his eyes met the pink hedgehog’s. “You know. I don’t have to do this. I can just tell everybody about your weird doll of Sonic.” Tails said, dropping Jamie’s painting, which struck a nerve. _That was expensive!_ Jamie's smile stretched, biting back any anger rising from his voice.

“I burned it.” Tails froze, obviously not expecting that which Jamie wasn’t either, but he was serious about nobody finding out. He'd be a laughing stalk. Jamie had then moved toward Tails, his hands stroking the yellow fox’s tails before moving them away from the view of his ass, which noticeably made the fox freeze.

“Besides, I’ve already got a new doll to play with.” He says against Tails’ fur suggestively and slowly using one of his hands to squeeze his ass.

“St-Stop that Jamie!” The fox growled, retracting from his touch which Jamie had expected. Jamie had stopped, feeling satisfaction in the fact of Tails being flustered.

“Let’s not drop any more paintings now, hm?” He said while giving the smaller fox a pat on the top of his head. Turning to sit back and relax by watching Tails reorganize and decorate his house. Jamie loved interior design, especially when he did it himself. However this time he was willing to make an exception at Tails’ expense.

Though Jamie had noticed every time the fox had looked back to check if he was still watching him, he’d lower his tails and flash a look of contempt.This was least satisfying to him but Jamie attempted to ignore. At least this was happening.

Rationalizing in his head that this was fine and that he needed to stop stressing, which the vanilla and lavender flavored air had certainly helped with that. After 40 minutes of watching Tails, Jamie began to grow hungry, already moving from his seat to head to the kitchen. He figured Tails probably needed a break. “I’ll make us something okay?” He said as he moved past Tails, the yellow fox only mumbling something in reply, still very angry.

Jamie had decided to just make themselves sandwiches, nothing special. Though, he might’ve put in an extra slab of ham for Tails. After all Jamie knew how much Tails loved meat. _The night of the incident was proof enough of that since he couldn't keep his eyes off of mine…_ He thought snarkily in his head.

While putting the finishing touches on the sandwiches an eerie shatter sent Jamie’s heart spiraling. He looked up, eyes meeting Tails as he stood in front of a shattered pot. Jamie would've been irritated but not furious if it was just a flower vase, but he had a look of horror as he realized it was one of his favorite artifacts.

Tails didn’t show any remorse and or care from doing this, he only let out a soulless, “Oops…”

“What the fuck?!” Jamie shouted, he took extreme pride in the historical discoveries over the years. So for it to just be smashed to pieces purposefully it made his calm and mature persona shatter just like the pot on his floor. He stormed toward Tails, Tails looking as angry as him.

“Why did you do that?!”

“It’s not my fault you don’t put important things in a display case.” He said, crossing his arms.

“You deliberately broke it!” Jamie's voice elevated.

“Yeah so what?”

Immense anger clouded Jamie’s better judgement. Making the pink hedgehog grab Tails by the arm, the fox refusing with surprise and anger, but Jamie didn’t care. He threw him onto the couch, ignoring his confused shouts of anger before using his body to hold Tails down. “Jamie what the fuck are you doing?!- Ouch stop that!” Tails squirmed as the weight of the hedgehog made it difficult for him to move.

“You've been asking for it this you bratty little asshole!” Jamie growled.

He had grabbed Tails by the tails harshly, shoving aside the fabric of his skirt before winding his palm backwards and smacking it right down on his ass. Tails letting out a loud cry in both pain and confusion, especially as Jamie had kept repeating the action over and over again. Jamie didn't think about Tails' screaming in the moment, even as they progressed into crying. He just kept doing it until he no longer felt the strength and or energy to do so anymore after his anger had subsided. 

And once he was no longer angry, all he could hear were the muffled sobs coming from Tails. He looked at him, wanting to feel satisfaction from this, but instead he just felt immediate regret-ah shit.

He fucked up.

Jamie let go of Tails’ tails, the fox curling up in a ball as expected. He felt horrible. He waited a few seconds before the fox had quieted down, Jamie let out a rush of air as he pushed his bangs out of his face briefly. “That was horrible of me Tails, I’m sorry.” He notices the fox is unmoving which makes the pink hedgehog finally decide. “Let’s just forget any of this happened, you don’t have to be my servant or whatever.”

It was a few moments until Tails unravelled his tails away from his face. “Why did you have to spank me? And-And be weird-and creepy?" He asked through choked breaths.

Jamie blushed with shame, feeling put on the spot before sighing. “I’m just upset about you seeing me in my room the other night.” Tails begins to sit up looking at Jamie as he continues. 

“I should’ve just talked to you like a normal adult.”

He nodded, still abnormally quiet until he said. "I do promise not to tell anybody Jamie..." Tails said which Jamie appreciated.

The pink hedgehog nodded before speaking up. "I promise I won't tell people you're a peeping tom."

Tails smiled at that and gave a sigh of relief. Jamie smiled as well and he had spoken once more without thinking. "Oh and I won't tell anybody about your crush on Sonic." The fox's head snapped toward him, his eyes narrowing.

"You really are a creep aren't you?" Tails said, which normally Jamie would've felt insulted by, but after putting the fox in a literal maid outfit and spanking him...yeah he was starting to see it.

"At least that's something we have in common."

"Yeah except that Sonic prefers me over you." The spiteful tone in his voice surprised Jamie. "No-No he doesn't." Jamie said incredulously.

"Jamie, he said he'd rather cripple himself than hang out with you." Tails said with a smug smile.

Ouch.

He didn't deny that Sonic didn't like him, but that still kinda hurt.

"Oh yeah? Then why has he been ignoring you the majority of the month?" He asked, a little irritated.

Tails' mouth opened to say something but no words came out of his mouth, he was speechless. "Face it fox, Sonic isn't into either one of us." Jamie said. He had already come within terms with it. Though he still couldn't let go of his admiration for the blue hedgehog. It appeared that Tails was also having a harder time accepting it as well.

He couldn't see the fox's face as it was lowered, Jamie noticed his fist was clenched against his thighs, which was a telltale sign of either Tails crying or Tails going off on an outburst. One thing for sure Jamie knew was he needed comfort, so he slowly placed a hand on Tails' back and rubbed the fox gently.

He felt the tension from his back melt away after a few moments of continuing this.

"I'm just tired of being ignored." Tails suddenly said, leaning closer into Jamie's touch.

"Tails, you're always welcome in my house. Sonic may ignore us both, but at least we have each other."

"Ew."

The pink hedgehog rolled his eyes. Why did he even bother…

He started to move his hand away from Tails, which the fox looked offended by. "H-Hey keep going."

Jamie looked at him peculiarly before placing his hand on his back once more. Applying pressure to his back with his thumbs he noticed the fox shuddering from his touch which made the hedgehog feel conflicting feelings. It didn't help at all since the incense he had fogged the entire house, making it near impossible to stray away from those kinds of thoughts. He intentionally chose lavender and vanilla aromas to calm himself down, after all the effects of which were supposed to help with anxiety and calm the mind, but he'd also forgotten both lavender and vanilla were also for arousal.

He heard a soft sound coming from Tails which Jamie could only identify as a purr. "Wow you're really needy." Jamie muttered, stopping for a second to re-adjust his position on the couch so Tails was essentially between his legs as Jamie massaged him. He didn't mind his own shoes on his couch, too busy thinking about how cute Tails looked from this angle. Tails occasionally glanced back at Jamie, fervently biting his bottom lip as he casted a look that Jamie could describe as lust. The aromatherapy was getting to him too.

"Did you like it?" Jamie asked out of the blue. Making Tails' relaxed ears perk suddenly.

"L-Liked what…?"

"Liked me spanking you?" Tails pauses for a moment, not answering. 

Well only one way to find out. 

Jamie had moved away from Tails to turn before grasping both of Tails' hips easily, him being much smaller than him and bent him over across his lap. He noticed a gasp as the fox's face hit the cushion. "Jamie?!" The way Tails said his voice only made Jamie more encouraged to try.

He grabbed him by the tails with one hand, which he was rewarded with another gasp. Jamie rubbed and groped his ass for a moment, it was just as soft and plump as before. He squeezed it briefly and started wiggling it in his hands. 

“Where did you get all this cake from Tails?” He asked, smiling down on him. Tails however didn’t seem pleased with this and had wrapped his hand over Jamie's wrist as an attempt to stop. "Jamie." He warned with a growl but Tails didn't move his hand away. In fact he prompted it to keep rubbing his soft ass.

Jamie took a moment or two to rub it before giving a firm slap on his ass, Tails squawked before trembling and gasping. He looked at the fox intently, making sure he didn't cross a line as he said nothing. Jamie squeezed his ass gently before repeating with the same amount of force each time. As he did this he felt Tails rubbing his thighs together from each slap he received, letting out small noises. "You like this?"

Tails didn't reply, still rubbing his thighs on Jamie.

"You like getting spanked by me huh Tails?" He kept going, still slapping his ass harder. "Do you think about Sonic spanking you Tails?"

He could hear the fox whimpering, as an attempt to contain himself.

“You really are a pervert huh?” Jamie said, his slaps starting to get harder as he watched the fox crumble. Tails' hands dug into Jamie's cushions as his mouth had widened and his panting becoming louder. Jamie started to tug on his tails to lift them up more as he spanked him, he wanted to keep teasing him. "You naughty fox. What would Sonic think if he saw you like this? If he saw his little friend getting spanked by me instead of him?" He had felt something warm trail down his legs suddenly after a few more spanks. Jamie paused for a moment to examine it, quickly realizing it was precum.

His brows raising as he looked at Tails, the small fox becoming flustered.

"Mhhph- Jamie I think I should go." Tails finally said, his body still shaking and trembling. He got up, on all fours, attempting to stand up until Jamie had kept him still as he still firmly held his tails. Jamie had moved his legs on the couch once more, his groin directly besides the yellow fox's ass. He used his free hand to begin stroking his dick as it prodded out of his fur.

Tails said in that small whiny tone. "Jamie." His eyes had closed as Jamie had started to stroke his erection against his fat ass. "Shh, Tails this is almost perfect. I know how much you want this." He said softly, resting his long cock between his asscheeks. Sliding up and down for a few moments, watching Tails shake even more.

His soft ass surrounded his cock, making the hedgehog tremble, especially as Tails had bucked his ass closer against his groin. 

He started squeezing his ass with one hand and the other to pull his tails. "Jamie!" Tails gasped, nearly sending the pink hedgehog over the edge before coming to an abrupt stop. He didn't want to cum so soon, so instead he had his groin move away and out of reach from Tails. Making the fox whimper briefly as Jamie laid on his back.

Tails looked as if he was going to attempt to leave again, but Jamie had hooked his arms around his waist to bring his ass closer to him. Jamie rubbed his face against his soft and round ass. "Why don't you give my cock a goodbye kiss before you leave?" He said as he lifted his face from his rear. Noticing the fox's scowl and said as reassurance. "I promise I'll let you go and we can forget this ever happened, okay?"

Tails held his gaze for a bit before turning his head back. Just as Jamie felt as if Tails was just gonna leave again, instead he felt a firm hand grasping his dick. 

"Just...For a minute okay?"

  
  


***

Tails didn't think he'd get that far, and once he did he was surprised with himself how much he had actually enjoyed sucking dick. 

"Just for a minute huh?" Tails overheard Jamie as he pushed his cock deeper into his throat as he had gotten used to it. His pink friend's hands were prying his ass wide. His warm tongue licking up and down inside of his entrance as he sucked. Tails had gripped harder on Jamie's fur as he bobbed up and down on his cock faster, moaning with his cock still in his mouth.

Jamie took his mouth off of Tails which made him whimper. Though he could feel his rapid hot breaths against his moist ass. "Sonic's definitely missing out." He moaned, his eyes squeezing before he had thrusted upward into Tails' mouth, making him gag. It was harder to pull away as he felt Jamie's hand forcing his head down further making him stay still so he could properly fuck his throat. Tail's throat burned as Jamie violated his mouth. He pinched Jamie's thigh as hard as he could to make him stop.

With a couple of more thrusts the hedgehog hissed and finally let go, leaving the fox choking on air, his chest heaving as he shakily took the time to breathe.

He licked his lips rapidly as he tasted some salt from Jamie before noticing him changing position. He had sat up, connecting his groin closely against Tails. Moving him in front of him, on his lap again, moist cock rubbing against Tails' thighs.

"I'm only here until you cum, ok?" Tails breathed, trying to ignore his heated body from his fur and not to mention the added weight of the dress.

His body pulsated even more as Jamie's hands clasped onto the side of his ass once again. An idle burn reminding him how good it felt being spanked previously. He missed it, but he was afraid to admit it. He just focused his attention on the pillow lying in front of him. Jamie had finally answered, amusement in his tone. "Whatever you say Tails." His ass stung sharply as he received a slap, jiggling in the process.

"Ah!" Tails cried as he received another with more impact. Blinking rapidly as tears stung his eyes as both his ass and cock ached, his member started to extend from his body.

"Tell me what you want me to do to you." Jamie said, his face diving into the crook of Tails' neck. His breath hot and heavy against his neck, making Tails shudder. This and Jamie's hands pinching his ass made it hard for the fox to form the words.

He thought he wanted to leave, but now all he could think about was Jamie fucking him.

Jamie has rotated his hips toward Tails, grinding his cock against his cheeks while sucking on his neck. 

Tails moaned incoherently, his brain turning to mush the more he breathed the air. "Agh...mmm ...mhh…" His limbs trembled as he held himself up as best he could.

Jamie sucked and bit his neck, moving aside the maid dress to get access to his shoulder. With every bite he had received was followed up by a lick. His heart couldn't stop pounding from the overwhelming pleasure. 

"Pl-Please Jamie." He begged, his lips trembling more than before.

Jamie pulled away briefly, looking at him maliciously. "What was that? Use your big boy words." 

The fox's hands balled into fist once more onto the fabric of his clothes, he started rubbing himself against his dick. "J-Just fuck me already." Hoping he didn't need to repeat it he gripped onto Jamie's legs tightly. 

But Jamie didn't budge, instead he looped his hand around onto his chest, lowering the collar of the dress more to pinch his chest under his white fur. 

Resting his chin on his shoulder, he asks. "You want me to fuck you? What about Sonic? Aren't you saving yourself for him?" Tails could tell he was trying to work him up again. 

He bit his bottom lip before answering. "I-I don't really care about him now." Jamie froze for a bit, which was odd. It made the fox feel as though he was going to drag this out longer.

But out of nowhere Jamie had grabbed a hold of Tails' body, lifting him briefly. Applying spit onto his cock, rubbing along his length, as well as taking the time to rub around and finger Tails' entrance. Tails immediately clenched in the process, only taking a second or two to relax before Jamie had slipped the head of his penis into Tails. His chest moving rapidly as he felt his head stretch him when wasn't even halfway inside of him.

Tears threatened to sting his eyes as he allowed Jamie to penetrate him slowly. His heart thudding in his chest. Inch by inch Jamie's cock had sunk into his ass. Jamie had taken control and pushed Tails deeper into his couch, lifting his ass briefly so he could freely start moving inside of him. Jamie's cock filled his entire tight ass, making the fox rock his hips instinctively back and forth. Tails had held onto Jamie's nearest pillow to wrap his arms around it to smother his face.

He felt Jamie's dick pulsate from inside of him, the soft vibrations against Tails' walls as Jamie slowly moved inside of him made the fox shudder with arousal. 

"Fuck-Tails…" Jamie muttered, using his hands to lift his skirt up and making quick and slow thrusts into his soft and tight hole.

Tails was more vocal as Jamie had begun spanking once again and dirty talking. "Don't care about Sonic anymore hm?" He asked rhetorically in a soft tone, starting to thrust his throbbing hard dick a little more faster inside Tails. "Ever since that night you wanted to hop on my cock, right?"

Tails' heart sped as all he could think about was how good Jamie made him feel. His own cock hurt with the want to be stroked. "Were you thinking about touching yourself in that closet, Tails?" Jamie slammed into Tails suddenly, Tails trembling from how painful it felt at first. "Mmhph! J-Jamie!" He whined, lifting his face from the pillow briefly to suck in a breath.

Jamie paused for a moment, waiting for Tails for a second. "Keep going." He prompted, his jaws clenching again. He didn't realize he sounded like he wanted Jamie to stop.

Jamie waited a moment once more before thrusting into Tails again. More gentle than before which the fox appreciated but still missed how rough he went on him.

"You...You can be a little harder again." He looked behind him staring at Jamie.

Jamie looked hesitant, genuinely cautious about the possibility of hurting Tails again. "Are you sure?"

Tails nodded before pressing his face against the pillow once more.

He didn't expect Jamie to immediately go back to slamming hard inside of him.

"I didn't realize how much you liked it rough Tails." He said as he started fucking him faster.

Tails suddenly feels his chest compress against his head, pushing him more into the couch.

The pink hedgehog placed his legs on the inside of both of Tails' legs. Keeping his legs wide for him so it was easier to fuck him. The fox was left breathless as soon as his dick pounded into him mercilessly.

"That's right take that cock you little pervert." Jamie panted, his chest heaving tremendously as he fucked him. "Jamie!" Tails' sobs were muffled from the pillow. His cock felt so hot and warm as it moved so quickly inside of him. Tails' dick pulsated as it threatened to cum. He removed his face from the pillow, gasping as he looked back to watch Jamie's large cock fucking his asshole.

"Ah!- Oh fu-fuck!" Tails cried as Jamie had begun hitting the right spot with the addition of his ass being stretched and squeezed to the point of aching.

Suddenly he had felt Jamie's weight pressing the fox further into the cushions the deeper his dick pounded into him. The fox let out loud cries of pleasure. "Jamie!" He moaned his name louder, his eyes rolling to the back of his head as he felt him constantly thrusting into the right spot. The sound of his hips and balls smashing into him made Tails' heart race. "Yes! Yes!" He moaned while simultaneously bucking his ass into his thrusts as he took his hard cock.

"Oh fuck Tails. You feel so good!" Jamie moaned into his fur, his speed increasing. 

He suddenly felt his entire asshole fill with cum. The hot substance sticking to his walls as it filled his hole. There was so much, some had trailed outside of him, the hedgehog still fucking him as he came deep inside. With a few final thrusts as he had finally finished cumming he was satisfied. Jamie quickly becoming limp on top of him.

Tails let out a few muffled sounds as he squirmed, his friend's dick still inside of him. "J-Jamie...G-Get off." He grunted, he felt a little light headed still. His heart was thudding inside of his chest, he wanted more.

There was a moment or two of Jamie catching his breath before finally pulling himself out of Tails. Tails could feel the rest of his seed dripping out of his yellow ass, it oddly felt good to him.

Once Tails no longer felt Jamie's weight put on him,Tails turned over. However he wasn't expecting Jamie still on top of him looking down on him and his erection.

"Sorry I forgot about you." He said and without another word he had grabbed Tails' member. Tails winced at the sensitivity of his dick, it ached as Jamie's palm warmed it up. He spit on his cock, lubricating him as he started stroking up and down along the base.

Tails' eyes shut as he let Jamie jerk him off, his hands resting on his shoulders. "Mm-can you su-suck me?" Tails stuttered, his eyes wavering as he looked up at Jamie.

The pink hedgehog blinked at him and scoffed. "No."

"Please Jamie…" He pleaded, placing his hands together. "I-I'll actually be your servant this time. I'll do everything you say." He offered which immediately grabbed his attention.

"For a month?" Tails immediately nodded, he'd do anything. Suddenly feeling the couch shift as Jamie had moved, though this time he had turned around and flopped his half flaccid cock on Tails' face.

The fox blushed as he heard Jamie's command. "Suck, I can go for another round." He said, Tails moaning in agreement once he felt the tip of his penis being prodded with Jamie's tongue. He felt Jamie's dick press against his mouth as it gaped, which he gladly swallowed as much as he could. It being much saltier than before, due to probably his cum.

Tails' hands rub along Jamie's thighs as he sucked his cock. Losing himself in the motion of Jamie sucking his as well, while bucking his hip toward Tails' mouth.

Jamie's pace increased, slurping faster than before. Tails rocked his hips back and forth into his warm mouth, his eyes clenching shut as soon as he felt him begin to orgasm. 

He moaned against his cock, still being muffled out with his length still shoved in his mouth. He heard Jamie's coughing and felt a warm drip of saliva and presumably cum on his leg. As Tails high from his orgasm dissolved, he felt a whirlwind of pain inflicted in his throat again as Jamie started throat fucking him.

His own muffled sounds as well as his couch's springs grunting was the only thing Tails' could hear. Tails tried breathing through his mouth, but it was getting harder as time stretched out.

"Fuck!" Jamie cried with a final thrust once more before quickly slipping out of Tails' mouth and suddenly cumming.

Breathing rapidly as he felt his seed paint his entire face, Tails could taste the cum that had sprayed into his mouth, too breathless to reject any of it.

He heard Jamie letting out a deep moan in relief before rolling off of Tails. Tails could only lay there still gasping for air, his brain foggy from all of the overwhelming sensations he's felt and replayed them over in his brain.

He felt already worn down and used. His eyes fell shut only after a few moments of him clearing his throat. "That was better than imagining sex with Sonic." Jamie commented suddenly, Tails noticed he had turned himself to lay on his side facing Tails.

The yellow fox let out a dry cough before muttering. "Yeah...it was."

Silence stretched between them before Jamie looked over to him with some concern. "Are...you alright?" 

Tails' could only reply in a weak voice since his throat felt inflamed and sore. "I can taste the cum from my nose."

He received a laugh before Jamie had sat up. Staying still for a moment to catch his breath before asking him. 

"You want a sandwich?"

Tails just looked at him wearily, sucking in a breath before saying. "Yeah sure."

***

The last couple of following days after Tails were surprisingly nice. Tails was uncharacteristically following Jamie around, though maybe that had something to do with him being able to give something that Sonic couldn't. Jamie stressed the fact that he wasn't serious about Tails actually being his servant, though Tails seemed insistent over the idea. Jamie just didn't realize how much Tails liked being ordered around by him.

He also didn't realize how much he actually liked spending time with him? The looks their friends gave them whenever they hung out in a group and Tails ever offered to stick to Jamie made his entire skin on fire.

More specifically Sonic as he's grown a little more suspicious as the month went on.

So far as much as popping up into Jamie's house.

The pink hedgehog looked at the blue hedgehog standing in front of his house. Jamie crossed his arms, his brows lifting from his face as Sonic asked him. "Hey Jamie, is Tails with you?"

Jamie sighed, "Yes, yes he is." He said, looking the hedgehog up and down.

"What do you want?"

Sonic shuffled his feet a bit on the ground, looking downwards a bit as he answered. "I've uh noticed you and Tails, hanging out a lot." 

"Yes…" Jamie confirmed his words, urging him to go on as he looked up at him.

"I just wanted to ask, what's the deal with that?" Sonic asked, his brows furrowed in confusion.

"What do you mean?" Jamie placed his hands on his hips as he leaned against the doorframe. "It's...weird. Like normally he'd be asking me to hang out with him, but instead it's you." The tone of his voice changed as he gestured to him.

This is when Jamie had started to smile, folding his arms and crossing his legs, leaning further into the doorframe. 

"Ogilvie Maurice Hedgehog."

"I told you not to call me that." He gritted though Jamie ignored.

"Are you jealous?"

Sonic freezed for a moment, his eyes flickering a bit to avoid meeting the pink hedgehog’s gaze. "Of course not! That's ridiculous." He waved a dismissive hand.

"It's not like he's my best friend or anything and he's been avoiding talking to me and hanging out with me." He said passive aggressively which was just adorable to Jamie. "Ah, wouldn't know the feeling." He said smugly but just stood there as the hedgehog continued. "And it's not like he's been weirdly clinging onto you and been snooping around at suspicious times and it's not like he has really questionable clothes in his room."

"You found out about the playboy outfit too?" Sonic's eyes widened in alarm, Jamie couldn't help but hide behind his hand to smile as he chuckled. 

"Jamie...nothing is going on between you two right?" Sonic asked, his face filled with concern.

Jamie's smile began to disappear the longer he looked at Sonic's upset face, letting out a soft sigh. "Okay Sonic I'll let you in on a little secret." Jamie said at first, looking Sonic in the eyes as he said. "Tails has a crush on you."

Sonic blinked for a moment, his mouth taking an o shape as a reaction. 

"Yeah, it's kinda embarrassing for him. But that's why I'm helping him come within terms with it and move on. That's why we're hanging out together, I'm giving him dating advice." He lied, smiling at Sonic.

"Okay but that doesn't really explain the play-"

"He's a crossdresser Sonic, jeez you act like you've never seen one at comic con. Guy has his own kicks, let him be." Sonic shutted up after that, looking slightly relieved. "Ah...well good. I'm glad you're helping him Jamie. And hey, at least you two have something to talk about." He winked which made Jamie's smile widened. "Oh we have plenty to talk about indeed, bye Sonic." He waved politely as he began to close the door.

"Yeah, Cya James. Oh tell Tails I cleaned up his workshop for him." Sonic said before speeding off. That's a strangely nice thing for Sonic to do.

Man he's probably bored out of his mind. As Jamie shut the door, he walked back into his room where Tails was splayed naked on his bed restrained and blindfolded. 

"Who was that?" He asked while lifting his head despite not being able to see, perking up as Jamie entered the room. 

"Sonic." He answered with a sigh as he grabbed a bottle of lube before towering over Tails.

Tails laughed a bit. "What did he want?"

"He wanted to check up on you since he's jealous." Jamie started to cover his free hand with lube, as well as fingering his little fox friend's ass before grabbing a dragon dildo.

"Man, he needs other friends." Tails said before breaking out to whimper as Jamie carefully pushed it inside of him. "Oh you have no idea." Jamie said with a hum before leaning over Tails and giving him a peck on the forehead before giving him a smack on his ass, leaving a bright red mark.

"Now where were we?"


End file.
